Hotels with Swimming Pool in Windsor, Massachusetts

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Check availability on Windsor Hotels with Swimming Pool

Tonight
Jul 1 - Jul 2
Tomorrow
Jul 2 - Jul 3
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Top Windsor Hotels with Swimming Pool

Hotel Downstreet, Ascend Hotel Collection
Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1005)
"Very cute hotel. The room was huge and the staff were friendly. "
The price is P8,569
P9,571 total
includes taxes & fees
Jul 20 - Jul 21
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (392)
"Perfect for our needs"
The price is P12,165
P14,852 total
includes taxes & fees
Jul 13 - Jul 14
The Porches Inn at Mass MoCA
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (384)
"No frills but it was a great stay!"
The price is P4,836
P5,401 total
includes taxes & fees
Jul 10 - Jul 11
Sunset Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (664)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is P10,343
P12,340 total
includes taxes & fees
Jul 9 - Jul 10
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Ponds at Foxhollow
Indoor pool, outdoor pool

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The price is P13,107
P14,641 total
includes taxes & fees
Jul 13 - Jul 14
The Ponds at Foxhollow
Holiday Inn Express & Suites Pittsfield - Berkshires
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
The price is P11,774
P13,152 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P12,656
P14,137 total
includes taxes & fees
Jul 6 - Jul 7
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (747)
"Was great loved the jacuzzi tub "
The price is P5,577
P6,230 total
includes taxes & fees
Jul 6 - Jul 7
Howard Johnson by Wyndham Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What are some accommodations with pools in Windsor?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Red Roof Inn PLUS+ South Deerfield -- Amherst: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers a seasonal outdoor pool, an indoor pool, and buffet. Best Western Plus Berkshire Hills Inn & Suites: Offers 3 restaurants, an outdoor pool, and spa services. The Yankee, Trademark Collection by Wyndham: Provides free self parking, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Windsor?
Take a walk along the waterfront at Campers Beach and Iroquis Waterfront. Discover sights such as Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Swift River during your stay.
When is the best time to book a hotel with a pool in Windsor?
Taking into account the local weather in Windsor can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.